R3255

13-cis-Retinoic acid

≥98% (HPLC)

• Synonym(s): Isotretinoin
• Empirical Formula (Hill Notation): C₂₀H₂₈O₂
• CAS Number: 4759-48-2
• Molecular Weight: 300.44
• EC Number: 225-296-0
• MDL number: MFCD00079542
• PubChem Substance ID: 24278676

Properties

• assay: ≥98% (HPLC)
• form: powder
• technique(s): HPLC: suitable
• color: yellow to yellow-orange
• mp: 172-175 °C (lit.)
• storage temp.: −20°C
• SMILES string: [H]\C(C(O)=O)=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C
• InChI: 1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
• InChI key: SHGAZHPCJJPHSC-XFYACQKRSA-N
• Gene Information: human ... NOS2(4843) , RARA(5914) , RARB(5915) , RARG(5916)

Description

Application

13-cis-Retinoic acid has been used:

• as a component of fresh media for LA-N-5 differentiation
• to treat medulloblastoma cells for cell differentiation
• to treat spheroids for generating time-lapse videos
• to examine its head- deforming activity under light and dark conditions in Xenopus laevis

Packaging

100, 250, 500 mg in ampule

Biochem/physiol Actions

13-cis-Retinoic acid (RA) has anti-inflammatory and anti-tumor action. The action of RA is mediated through RAR-β and RAR-α receptors. RA attenuates iNOS expression and activity in cytokine-stimulated murine mesangial cells. It induces mitochondrial membrane permeability transition, observed as swelling and as a decrease in membrane potential, and stimulates the release of cytochrome c implicating mechanisms through the apoptosis pathway. These activities are reversed by EGTA and cyclosporin A. RA also increases MMP-1 protein expression partially via increased transcription.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R3255.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety Information

• Pictograms: GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H315 - H319 - H335 - H360
• Precautionary Statements: P201 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves